Hotels near Windham Vineyards and Winery

Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices

Check prices for these dates

Tonight
Jul 13 - Jul 14
Tomorrow
Jul 14 - Jul 15
Next weekend
Jul 18 - Jul 20
In two weeks
Jul 25 - Jul 27

Where to stay near Windham Vineyards and Winery?

Cave Mountain Motel
Stunning two-story home with a charming porch and beautifully manicured yard.

Cave Mountain Motel

2.5 star property
9.4 out of 10, Exceptional, (127)
The price is CA $190
CA $206 total
includes taxes & fees
Jul 15 - Jul 16
Cave Mountain Motel
Silas House
Relax in this inviting living room with a central sofa, side table, and armchair.

Silas House

3.0 star property
10.0 out of 10, Exceptional, (12)
The price is CA $248
CA $268 total
includes taxes & fees
Jul 15 - Jul 16
Silas House
Albergo Allegria Hotel & Breakfast Restaurant
Enjoy a meal at the dining table, with a view of the surrounding landscape through the large window.

Albergo Allegria Hotel & Breakfast Restaurant

3.5 star property
9.6 out of 10, Exceptional, (265)
The price is CA $199
CA $215 total
includes taxes & fees
Jul 15 - Jul 16
Albergo Allegria Hotel & Breakfast Restaurant
Eastwind Windham
Two-story house with a front entrance, wooden deck, and potted plants on the steps.

Eastwind Windham

2.0 star property
9.4 out of 10, Exceptional, (56)
The price is CA $329
CA $367 total
includes taxes & fees
Aug 12 - Aug 13
Eastwind Windham
Hotel Vienna
Escape to a serene retreat amidst lush greenery, with a spacious deck perfect for relaxation or entertaining.

Hotel Vienna

2.5 star property
9.4 out of 10, Exceptional, (588)
The price is CA $171
CA $185 total
includes taxes & fees
Aug 3 - Aug 4
Hotel Vienna
Antique Rose Inn Windham
Stunning two-story house with a charming porch and tower, surrounded by a serene winter landscape.

Antique Rose Inn Windham

3.0 star property
9.0 out of 10, Wonderful, (121)
The price is CA $185
CA $200 total
includes taxes & fees
Jul 16 - Jul 17
Antique Rose Inn Windham
Winwood Condominiums by Windham Mountain Club
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Winwood Condominiums by Windham Mountain Club

3.0 star property
8.6 out of 10, Excellent, (324)
Winwood Condominiums by Windham Mountain Club
Mountain Treasure B&B
Explore the serene rolling hills and vibrant autumn foliage along winding paths.

Mountain Treasure B&B

3.0 star property
9.4 out of 10, Exceptional, (273)
The price is CA $208
CA $225 total
includes taxes & fees
Jul 15 - Jul 16
Mountain Treasure B&B
Wylder Hotel Windham
Relax in this stylish room with two armchairs and a round table, offering a view of the outdoors through the large window.

Wylder Hotel Windham

3.5 star property
8.6 out of 10, Excellent, (61)
The price is CA $233
CA $320 total
includes taxes & fees
Aug 3 - Aug 4
Wylder Hotel Windham
Black Bear Lodge
Surrounded by trees and a mountain range, this riverside setting offers a tranquil atmosphere perfect for relaxation.

Black Bear Lodge

2.5 star property
9.0 out of 10, Wonderful, (114)
The price is CA $204
CA $220 total
includes taxes & fees
Jul 15 - Jul 16
Black Bear Lodge
The Colonial Motel
Step into the charm of The Colonial Motel, where a cozy porch with a swing invites relaxation.

The Colonial Motel

2.5 star property
9.4 out of 10, Exceptional, (362)
The price is CA $104
CA $115 total
includes taxes & fees
Jul 27 - Jul 28
The Colonial Motel
Moore's Motel
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Moore's Motel

2.5 star property
8.6 out of 10, Excellent, (145)
The price is CA $164
CA $177 total
includes taxes & fees
Jul 15 - Jul 16
Moore's Motel
Kaatskill Mountain Club at Hunter Mountain
Relax by the pool surrounded by comfortable lounge chairs and a small table.

Kaatskill Mountain Club at Hunter Mountain

2.0 star property
9.2 out of 10, Wonderful, (251)
The price is CA $259
CA $308 total
includes taxes & fees
Aug 12 - Aug 13
Kaatskill Mountain Club at Hunter Mountain
Hunter Lodge, a Bluebird by Lark
Cozy library space with a central table and bookshelves, perfect for reading or small gatherings.

Hunter Lodge, a Bluebird by Lark

3.0 star property
9.2 out of 10, Wonderful, (686)
The price is CA $178
CA $222 total
includes taxes & fees
Jul 28 - Jul 29
Hunter Lodge, a Bluebird by Lark
Beds on Clouds
Stroll through lush gardens surrounded by classic columns and vibrant flowers.

Beds on Clouds

3.0 star property
7.4 out of 10, Good, (67)
The price is CA $235
CA $253 total
includes taxes & fees
Jul 15 - Jul 16
Beds on Clouds
The Haüs Windham
Cozy attic bedroom with a large bathroom, bathtub, and comfortable bed.

The Haüs Windham

2.0 star property
8.6 out of 10, Excellent, (4)
The Haüs Windham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other landmarks in Windham

Ashland Town Hall

Ashland Town Hall is just one of the places to see in Ashland, so why not enjoy the other things to explore during your travels?

See properties in Ashland Town Hall
Ashland Town Hall

Frequently asked questions

How much does it cost to stay in a hotel near Windham Vineyards and Winery?
Visit Hotels.com, enter your search criteria, and sort by price to find the lowest prices available. Pricing varies based on where you plan to go and when.
  • Search for the lowest price per night from CA $104
What are the best hotels near Windham Vineyards and Winery?
  • Guests love staying at Hotel Mountain Brook, which is a hotel near Windham Vineyards and Winery.
  • Also highly rated is Urban Cowboy Lodge, which is in the larger area.
  • In fact, you'll have plenty of options to choose from with 2,643 hotels, vacation rentals, and other accommodations in the area.
What are the best things to see and do around my hotel near Windham Vineyards and Winery?
  • Sights like Windham Mountain Resort and Zoom Flume are in the area near Windham Vineyards and Winery.
How much does it cost to stay in a hotel near Windham Vineyards and Winery?
On Hotels.com, you can find a variety of room prices depending on when and where you plan to go. Simply sort by price on the search results and filter by your preferred criteria to find the best options for you and your budget.
  • Search for the lowest price per night from CA $104
Are all taxes and fees included in the prices shown on Hotels.com for hotels near Windham Vineyards and Winery?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.
Can I find hotels close to Windham Vineyards and Winery that are fully refundable?
Yes, there are many hotels with refundable room rates, but be sure to check the cancellation deadline. To find refundable rates, select the "Fully refundable" filter when searching for hotels.
What are the best romantic hotels near Windham Vineyards and Winery?
What are the best hotels close to Windham Vineyards and Winery with free breakfast?
  • Enjoy a free continental breakfast to begin your day at Hotel Mountain Brook, which is a 36-minute drive from Windham Vineyards and Winery.
  • Shandaken Inn is also a recommended place to stay with a free local cuisine breakfast, and it's located in the larger area.
What are the best family hotels close to Windham Vineyards and Winery?
  • Keep the family happy with a stay at Wylder Hotel Windham which offers free cribs, high chairs, and an outdoor pool. Windham Vineyards and Winery is a short drive away.
  • Also consider Riedlbauer's Resort as another great choice for your family's trip.
What are the best luxury hotels near Windham Vineyards and Winery?
  • Indulge yourself when you stay at Urban Cowboy Lodge, which is within reach of Windham Vineyards and Winery and offers a sauna and deep-tissue massages.
  • Another upscale property is AutoCamp Catskills, which is in the larger area.
What are the best hotels near Windham Vineyards and Winery with free parking?
  • Drive and park with ease when you stay at Hotel Mountain Brook, which offers free parking. You'll be a 36-minute drive from Windham Vineyards and Winery.
  • Urban Cowboy Lodge also has free parking and is in the larger area.
What are the best hotels near Windham Vineyards and Winery with a pool?
  • If swimming is at the top of your list, Wylder Hotel Windham has an outdoor pool. Windham Vineyards and Winery is a short 14-minute drive from the hotel.
  • Another great choice for a hotel with a pool is Shandaken Inn.
What cheap motels can I book close to Windham Vineyards and Winery?
  • To save on your stay near Windham Vineyards and Winery, take a look at Cave Mountain Motel, which offers a free buffet breakfast and parking.
  • Another inexpensive motel nearby to consider is Moore's Motel.
What are the best things to see and do around my hotel near Windham Vineyards and Winery?
  • Other attractions near Windham Vineyards and Winery include Windham Mountain Resort and Zoom Flume.
What are the best pet-friendly hotels close to Windham Vineyards and Winery?
Are all taxes and fees included in the prices shown on Hotels.com for hotels near Windham Vineyards and Winery?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.